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Preparation and characterization of isatin complexed with Cu supported on 4-(aminomethyl) benzoic acid-functionalized Fe3O4 nanoparticles as a novel magnetic catalyst for the Ullmann coupling reaction

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Abstract

Isatin complexed with Cu supported on 4-(aminomethyl) benzoic acid-functionalized Fe3O4 nanoparticles (Cu-IS-AMBA-MNPs) as a new catalyst was designed, prepared and characterized by appropriate analyses. The heterogeneous reusable catalyst was successfully used for the efficient and widespread syntheses of diaryl ethers and diarylamines via the Ullmann coupling reaction. This green catalyst was easily removed, reused several times with no significant loss of its activity, and provided a clean synthesis with excellent yield and reduced time.

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References

  1. J.S. Sawyer, Tetrahedron 56, 5045 (2000)

    Article  Google Scholar 

  2. X. Zhang, F. Liu, Z. Wei, Z.O. Wang, Lett. Org. Chem. 10, 31 (2013)

    CAS  Google Scholar 

  3. H.J. Cristau, P.P. Cellier, S. Hamada, J.F. Spindler, M. Taillefer, Org. Lett. 6, 913 (2004)

    Article  CAS  PubMed  Google Scholar 

  4. K.C. Nicolaou, C.N.C. Boddy, S. Brase, N. Winssinger, Angew. Chem. Int. Ed. 38, 2096 (1999)

    Article  CAS  Google Scholar 

  5. K.C. Nicolaou, S. Natarajan, H. Li, N.F. Jain, R. Huges, M.E. Solomon, J.M. Ramanujulu, C.N.C. Boddy, M. Takayanagi, Angew. Chem. Int. Ed. 37, 2708 (1998)

    Article  CAS  Google Scholar 

  6. Q. Zhang, D.P. Wang, X.Y. Wang, K. Ding, J. Org. Chem. 74, 7187 (2009)

    Article  CAS  PubMed  Google Scholar 

  7. F. Ullmann, Chem. Ber. Dtsch. Chem. Ges. 37, 853 (1904)

    Article  Google Scholar 

  8. A. Shaabani, S.E. Afshari, R. Hooshmand, A.T. Tabatabaei, F. Hajishaabanha, RSC Adv. 6, 18113 (2016)

    Article  CAS  Google Scholar 

  9. J. Lindley, Tetrahedron 40, 1433 (1984)

    Article  CAS  Google Scholar 

  10. J.C. Henrim, P.C. Pascal, H. Samy, F.S. Jean, Org. Lett. 6, 913 (2004)

    Article  CAS  Google Scholar 

  11. Y. Zhang, G. Ni, C. Li, S. Xu, Z. Zhang, X. Xie, Tetrahedron 71, 4927 (2015)

    Article  CAS  Google Scholar 

  12. S. Handa, Y. Wang, F. Gallou, B.H. Lipshutz, Science 349, 1087 (2015)

    Article  CAS  PubMed  Google Scholar 

  13. J.Y. Kim, J.C. Park, A. Kim, A.Y. Kim, H.J. Lee, H. Song, K.H. Park, Eur. J. Inorg. Chem. 28, 4219 (2009)

    Article  CAS  Google Scholar 

  14. K. Huang, Y. Chen, J.H. Chan, L.R. Mike, D.L. Robert, Synlett 10, 1419 (2011)

    Article  CAS  Google Scholar 

  15. V.R. Choudhary, D.K. Dumbre, P.N. Yadav, S.K. Bhargava, Catal. Commun. 29, 132 (2011)

    Article  CAS  Google Scholar 

  16. S.A.R. Mulla, S.M. Inamdar, M.Y. Pathan, S.S. Chavan, Tetrahedron Lett. 53, 1826 (2012)

    Article  CAS  Google Scholar 

  17. F. Zhou, J. Guo, J. Liu, K. Ding, S. Yu, Q. Cai, J. Am. Chem. Soc. 134, 14326 (2012)

    Article  CAS  PubMed  Google Scholar 

  18. S.G. Babu, R. Karvembu, Tetrahedron Lett. 54, 1677 (2013)

    Article  CAS  Google Scholar 

  19. R.K. Gujadhur, C.G. Bates, D. Venkataraman, Org. Lett. 3, 4315 (2001)

    Article  CAS  PubMed  Google Scholar 

  20. F.Y. Kwong, A. Klapars, S.L. Buchwald, Org. Lett. 4, 581 (2002)

    Article  CAS  PubMed  Google Scholar 

  21. H.J. Cristau, P.P. Cellier, J.F. Spindler, M. Taillefer, Org. Lett. 6, 913 (2004)

    Article  CAS  PubMed  Google Scholar 

  22. S. Zhang, D. Zhang, L.S. Liebeskind, J. Org. Chem. 62, 2312 (1997)

    Article  CAS  PubMed  Google Scholar 

  23. A.A. Kelkar, N.M. Patil, R.V. Chaudhari, Tetrahedron Lett. 43, 7143 (2002)

    Article  CAS  Google Scholar 

  24. A.S. Gajare, K. Toyota, M. Yoshifuji, F. Yoshifuji, Chem. Commun. 17, 1994 (2004)

    Article  CAS  Google Scholar 

  25. E. Buck, Z.J. Song, D. Tschaen, P.G. Dormer, R.P. Volante, P.J. Reider, Org. Lett. 4, 1623 (2002)

    Article  CAS  PubMed  Google Scholar 

  26. C. Palomo, M. Oiarbide, R. Lopez, E. Gomez-Bengoa, Chem. Commun. 19, 2091 (1998)

    Article  Google Scholar 

  27. D. Ma, Q. Cai, Org. Lett. 5, 3799 (2003)

    Article  CAS  PubMed  Google Scholar 

  28. N.K. Ojha, G.V. Zyryanov, A. Majee, V.N. Charushin, O.N. Chupakhin, S. Santra, Coord. Chem. Rev. 353, 1 (2017)

    Article  CAS  Google Scholar 

  29. J.S. Zheng, X.S. Zhang, P. Li, J. Zhu, X.G. Zhou, W.K. Yuan, Electrochem. Commun. 9, 895 (2007)

    Article  CAS  Google Scholar 

  30. W. Wu, Q. He, C. Jiang, Nanoscale Res. Lett. 3, 397 (2008)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  31. A. Wang, X. Liu, Z. Su, H. Jing, Catal. Sci. Tech. 4, 71 (2014)

    Article  Google Scholar 

  32. S. Fan, W. Dong, X. Huang, H. Gao, J. Wang, Z. Jin, J. Tang, G. Wang, ACS Catal. 7, 243 (2016)

    Article  CAS  Google Scholar 

  33. K. Mishra, T.N. Poudel, N. Basavegowda, Y.R. Lee, J. Catal. 344, 273 (2016)

    Article  CAS  Google Scholar 

  34. H.N. Dadhania, K.R. Dipak, N.D. Abhishek, Catal. Sci. Tech. 5, 4806 (2015)

    Article  CAS  Google Scholar 

  35. X. An, D. Cheng, L. Dai, B. Wang, H.J. Ocampo, J. Nasrallah, X. Jia, J. Zou, Y. Long, Y. Ni, Appl. Catal. B 206, 53 (2017)

    Article  CAS  Google Scholar 

  36. M.A. Zolfigol, V. Khakyzadeh, A.R. Moosavi-Zare, A. Rostami, A. Zare, N. Iranpoor, R. Luque, Green Chem. 15, 2132 (2013)

    Article  CAS  Google Scholar 

  37. M. M. Khodaei, A. Alizadeh, M. Haghipour, Res. Chem. Inter. (2017). https://doi.org/10.1007/s11164-017-3008-2

    Article  Google Scholar 

  38. K. He, Y. Ma, B. Yang, C. Liang, X. Chen, C. Cai, Mol. Biomol. Spectrosc. 173, 82 (2017)

    Article  CAS  Google Scholar 

  39. S. Liu, H. Wang, L. Chai, M. Li, J. Coll. Inter. Sci. 478, 288 (2016)

    Article  CAS  Google Scholar 

  40. R. Mirzajani, S. Ahmadi, J. Ind. Eng. Chem. 23, 171 (2015)

    Article  CAS  Google Scholar 

  41. M.A. Rahman, U. Culsum, A. Kumar, H. Gao, N. Hu, Int. J. Biol. Macromolec. 87, 488 (2016)

    Article  CAS  Google Scholar 

  42. D. Yang, J. Hu, S. Fu, J. Phys. Chem. C 113, 7646 (2009)

    Article  CAS  Google Scholar 

  43. R. Singh, B.K. Allam, D.S. Raghuvanshi, K.N. Singh, Tetrahedron 69, 1038 (2013)

    Article  CAS  Google Scholar 

  44. J.C. Vantourout, R.P. Law, A. Isidro-Llobet, S.J. Atkinson, A.J. Watson, J. Org. Chem. 81, 3942 (2016)

    Article  CAS  PubMed  Google Scholar 

  45. A. Ghorbani-Choghamarani, Z. Taherinia, Z. New J. Chem. 41, 9414 (2017)

    Article  CAS  Google Scholar 

  46. L. Cai, X. Qian, W. Song, T. Liu, X. Tao, W. Li, X. Xie, Tetrahedron 70, 4754 (2014)

    Article  CAS  Google Scholar 

  47. J. Liu, D. Yang, X. Yang, M. Nie, G. Wu, Z. Wang, P. Gong, Bio. Med. Chem. 25, 4475 (2017)

    Article  CAS  Google Scholar 

  48. K. Kulangiappar, M. Anbukulandainathan, T. Raju, Synth. Commun. 1, 2494 (2014)

    Article  CAS  Google Scholar 

  49. S. Yamada, M. Ishikawa, C. Kaneko, Chem. Pharm. Bull. 23, 2818 (1975)

    Article  CAS  Google Scholar 

  50. A. Kumar, B.S. Bhakuni, C.D. Prasad, S. Kumar, S. Kumar, Tetrahedron 69, 5383 (2013)

    Article  CAS  Google Scholar 

  51. H. Xu, Y. Chen, Synth. Commun. 37, 2411 (2007)

    Article  CAS  Google Scholar 

  52. F. Damkaci, C. Sigindere, T. Sobiech, E. Vik, J. Malone, Tetrahedron Lett. 58, 3559 (2017)

    Article  CAS  Google Scholar 

  53. M. Khalilzadeh, A. Hosseini, A. Pilevar, Eur. J. Org. Chem. 8, 1587 (2011)

    Article  CAS  Google Scholar 

  54. R. Arundhathi, D. Damodara, P.R. Likhar, M.L. Kantam, P. Saravanan, T. Magdaleno, S.H. Kwon, Adv. Syn. Catal. 353, 1591 (2011)

    Article  CAS  Google Scholar 

  55. S. Verma, N. Kumar, S.L. Jain, Tetrahedron Lett. 53, 4665 (2012)

    Article  CAS  Google Scholar 

  56. X. Liu, S. Zhang, Synlett 2, 268 (2011)

    Google Scholar 

  57. B. Kaboudin, Y. Abedi, T. Yokomatsu, Eur. J. Org. Chem. 33, 6656 (2011)

    Article  CAS  Google Scholar 

  58. J.C. Antilla, S.L. Buchwald, Org. Lett. 3, 2077 (2001)

    Article  CAS  PubMed  Google Scholar 

  59. M.L. Kantam, G.T. Venkanna, C. Sridhar, B. Sreedhar, B.M. Choudary, J. Org. Chem. 71, 9522 (2006)

    Article  CAS  PubMed  Google Scholar 

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Acknowledgement

We thank the Research Council of Razi University for generous financial support of this work.

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Correspondence to Mohammad Mehdi Khodaei.

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Khodaei, M.M., Alizadeh, A. & Haghipour, M. Preparation and characterization of isatin complexed with Cu supported on 4-(aminomethyl) benzoic acid-functionalized Fe3O4 nanoparticles as a novel magnetic catalyst for the Ullmann coupling reaction. Res Chem Intermed 45, 2727–2747 (2019). https://doi.org/10.1007/s11164-019-03760-0

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